A second-generation synthesis of polypyrrolinone nonpeptidomimetics: prelude to the synthesis of polypyrrolinones on solid support

A B Smith 3rd; H Liu; R Hirschmann

doi:10.1021/ol0059293

A second-generation synthesis of polypyrrolinone nonpeptidomimetics: prelude to the synthesis of polypyrrolinones on solid support

Org Lett. 2000 Jul 13;2(14):2037-40. doi: 10.1021/ol0059293.

Authors

A B Smith 3rd¹, H Liu, R Hirschmann

Affiliation

¹ Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.

PMID: 10891224
DOI: 10.1021/ol0059293

Abstract

[reaction: see text] A second-generation asymmetric synthesis of polypyrrolinones (3) has been achieved exploiting scalemic alpha-aminolactones (1) as building blocks. Imine formation between an appropriate lactone (1) and aldehyde (2), followed in turn by pyrrolinone ring construction promoted by KHMDS in the presence of 18-crown-6 and modified Swern oxidation furnished pyrrolinone aldehyde 3. This iterative, efficient three-step protocol paves the way for the synthesis of polypyrrolinones on solid support.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Aspartic Acid Endopeptidases / antagonists & inhibitors*
Dimethyl Sulfoxide
HIV Protease Inhibitors / chemical synthesis*
HIV Protease Inhibitors / pharmacology
HIV-1 / enzymology*
Oxidation-Reduction
Pyrrolidinones / chemical synthesis*
Pyrrolidinones / chemistry

Substances

HIV Protease Inhibitors
Pyrrolidinones
Aspartic Acid Endopeptidases
Dimethyl Sulfoxide

Grants and funding

GM-41821/GM/NIGMS NIH HHS/United States